N-bromobutanimide → 5-Bromo-4-chloro-6-(2-phenylethynyl)pyridin-2-amine

HRID 535388Notes

Reaction equation

HRID 535388 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]#[C:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[N:5]=[C:4]([NH2:16])[CH:3]=1.C1C(=O)N([Br:24])C(=O)C1>C(#N)C>[Br:24][C:7]1[C:2]([Cl:1])=[CH:3][C:4]([NH2:16])=[N:5][C:6]=1[C:8]#[C:9][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 866943684-Chloro-6-(2-phenylethynyl)pyridin-2-amine

Product 1

HCID 866943735-Bromo-4-chloro-6-(2-phenylethynyl)pyridin-2-amine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 4-chloro-6-(2-phenylethynyl)pyridin-2-amine B3a (1.0 g, 4.37 mmol), NBS (778 mg, 4.37 mmol) and ACN (20 ml) is stirred for 3 h at RT in the dark. The mixture is concentrated in vacuo and the product purified NP chromatography. Yield: 1.0 g (74%). HPLC-MS: M+H=307/309.

Workup

  1. concentrationThe mixture is concentrated in vacuo
  2. customthe product purified NP chromatography

Sources & evidence

ORD record
ord-353c3fa3196042598fd525898b4361c0
Source dataset
uspto-grants-2014_10
Patent number
US08859541B2

Reaction notes

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